Name: (4R)-4-Azido-L-proline
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

(R)-4-Azido-L-proline; H-Pro(4-N3) (2S,4R); H-L-Pro(4-N3) (2S,4R); H-L-Pro(4-N3)-OH (2S,4R); H-Pro(4-N3)-OH (2S,4R); (2S,4R)-H-L-Pro(4-N3)-OH

IUPAC Name

(2S,4R)-4-azidopyrrolidine-2-carboxylic acid

Canonical SMILES

C1[C@H](CN[C@@H]1C(=O)O)N=[N+]=[N-]

InChI

InChI=1S/C5H8N4O2/c6-9-8-3-1-4(5(10)11)7-2-3/h3-4,7H,1-2H2,(H,10,11)/t3-,4+/m1/s1

InChIKey

PPRFZPZRQYPCER-DMTCNVIQSA-N

Melting Point

153-157°C

Appearance

White crystalline powder

Storage

Store at 2-8 °C

(4R)-4-Azido-L-Proline hydrochloride, a versatile compound with diverse applications in biochemistry, plays a pivotal role in various fields. Here are four key applications presented with high perplexity and burstiness:

Protein Engineering: Utilizing (4R)-4-Azido-L-Proline hydrochloride in protein engineering, researchers can strategically introduce azide groups into proteins, enabling precise site-specific labeling and modification via click chemistry reactions. This sophisticated approach is essential for probing protein structure, function, and interplay, shedding light on the intricate world of biomolecular interactions.

Chemical Biology: In the domain of chemical biology, (4R)-4-Azido-L-Proline hydrochloride acts as a foundational element for crafting modified peptides and proteins. The azido moiety facilitates bioorthogonal reactions, empowering the investigation of biological phenomena in living organisms. By leveraging this compound, scientists can explore complex biological systems and unravel the underlying mechanisms governing life's processes.

Drug Development: The incorporation of (4R)-4-Azido-L-Proline hydrochloride into peptide-based drugs marks a groundbreaking advancement in therapeutic development. Enhancing the stability and efficacy of therapeutic peptides, this compound significantly improves the pharmacokinetic and pharmacodynamic properties of novel drugs. This innovative application holds great promise for designing next-generation therapeutics with enhanced efficacy and safety profiles.

Bioconjugation: Embarking on bioconjugation endeavors, researchers harness the potential of (4R)-4-Azido-L-Proline hydrochloride as a versatile linker for conjugating biomolecules, such as antibodies, nucleic acids, and small molecules. Through this strategic coupling, multifunctional bioconjugates are synthesized for diagnostic and therapeutic uses, enabling targeted drug delivery and molecular imaging. These bioconjugates represent a cornerstone in the realm of precision medicine and personalized healthcare.

1. Paroxetine hydrochloride

David Germann, George Ma, Feixue Han, Anna Tikhomirova Profiles Drug Subst Excip Relat Methodol. 2013;38:367-406. doi: 10.1016/B978-0-12-407691-4.00008-3.

Paroxetine hydrochloride (3S-trans)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-piperidine hydrochloride (or (-)-(3S,4R)-(4-(p-fluorophenyl)-3-[[3,4-(methylenedioxy)-phenoxy]methyl]piperidine hydrochloride), a phenylpiperidine derivative, is a selective serotonin reuptake inhibitor. Paroxetine is indicated for the treatment of depression, generalized anxiety disorder, obsessive-compulsive disorder, panic disorder, posttraumatic stress disorder, and social anxiety disorder. The physicochemical properties, spectroscopic data (1D and 2D NMR, UV, FT-IR, MS, PXRD), stability, methods of preparation and chromatographic methods of analysis of pharmaceutical, and biological samples of paroxetine are documented in this review. Pharmacokinetics, metabolism, and pharmacological effects are also discussed.

2. (3S,4R)-4-(4-Fluoro-phen-yl)-3-(hydroxy-meth-yl)piperidinium chloride

M Nirmala, B R Sreekanth, Peddy Vishweshwar, J Moses Babu, Y Anjaneyulu Acta Crystallogr Sect E Struct Rep Online. 2008 Apr 4;64(Pt 5):o800. doi: 10.1107/S1600536808008593.

The title compound, C(12)H(17)FNO(+)·Cl(-), is a degradation impurity of paroxetine hydro-chloride hemihydrate (PAXIL), an anti-depressant belonging to the group of drugs called selective serotonin reuptake inhibitors (SSRIs). Similar to the paroxetine hydro-chloride salt with protonation having taken place on the basic piperidine ring, the degradation impurity also exists as the hydro-chloride salt. The cyclic six-membered piperidinium ring adopts a chair conformation with the hydroxy-methyl and 4-fluoro-phenyl groups in the equatorial positions. The ions form a tape along the b axis through charge-assisted N(+)-H⋯Cl(-) hydrogen bonds; these tapes are connected by O-H⋯Cl(-) hydrogen bonds along the a axis.

3. Serotonin-1A receptor dependent modulation of pain and reward for improving therapy of chronic pain

Darakhshan Jabeen Haleem Pharmacol Res. 2018 Aug;134:212-219. doi: 10.1016/j.phrs.2018.06.030. Epub 2018 Jun 30.

Chronic pain conditions such as low back pain and osteoarthritis are the most prominent causes of disability worldwide. Morphine and other opioid drugs are the gold standard treatment for severe pain, including surgical pain, but the use of these drugs for chronic pain is limited largely because long term use of these drugs is associated with drug abuse and hyperalgesia which produces a negative impact on the treatment. Non-addictive treatments for chronic pain are, therefore, highly needed. Commonly used opioid drugs activate mu opioid receptors, resulting in an inhibition of tonic activity of nociceptive neurons. The rewarding effects of opioid drugs are also mediated via activation of mu opioid receptors and inhibition of GABA mediated control of the activity of dopamineregic neurons. Enhanced glutamate release and greater activity of NMDA glutamate receptors is linked to the hyperalgesic effects of opioid drugs. Evidence suggests that activation of serotonin (5-hydroxytryptamine; 5-HT)-1 A receptors modulates dopamine neurotransmission to inhibit rewarding effects of drugs of abuse. Activation of these receptors inhibits glutamate release from the sensory neurons to reduce pain transmission. To help develop strategies for improving therapeutics in chronic pain, and draw research interest in the synthesis of non-addictive opioid drugs which do not predispose to hyperalgesia, the present article concerns the potential mechanism involved in 5-HT-1 A receptor mediated inhibition of pain and reward.